At their high school reunion, Jill tries to avoid Joanie Graham, her high school friend who stole her boyfriend, and Tim and Jack try to fix the amplifier. Meanwhile, Al watches the boys and Brad’s girlfriend Ashley.
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Jill's sister Carol is having a baby girl. When they talk about the baby's name and Jill is going through the boys' baby toys, she wishes she could have a baby girl. Tim tells Randy and Brad that Jill always wanted a girl so they tell Mark that Jill wished he had been a girl. This upsets Mark and when Jill wants to bake a cake with him, he doesn't want to. When she finds out the truth, she tells Mark that what Randy and Brad told him isn't true. Tim is also upset because he doesn't want another child. But he feels alright again when Jill tells him that they don't have the time for another child.
At Al's 35th birthday, he wants a wife and kids, so Jill fixes him up with Ilene Markham. Al finds out that Ilene wants kids too, so he proposes to her on Tool Time. Randy and Brad write a letter to Mark pretending to be Isaiah Thomas, so Tim and Jill tell Mark to get revenge.
Tim stops telling jokes and screwing up on Tool Time after he installs an intercom and hears Randy call him a screw up. Brad wants to read "David Copperfield" so he can talk to it to Jennifer, but he finds out it's not about the magician and Jennifer breaks up with him.
Tim has trouble with Joe Morton, his new neighbor, after Joe dents part of his hot rod. Jill becomes good friends with Marie Morton, Joe's wife. Brad signs up for home ec. as his elective to meet girls, but when the other boys in school find out about his plan, it doesn't work out the way he planned.
Tim is afraid to cry after Mr. Binford, his boss and close friend, passes away.
It's Halloween and as usual, Tim is up to his old tricks, however Jill plans a prank of her own. Tim gets flowers from a fan named Rose but soon strange things start happening. She keeps calling him, Wilson thinks she is obsessed with him, Tim tries to hide but it's no use.
Tim accidentally blows up a bad picture of Jill for her library fundraising dinner. Meanwhile, Al takes the boys miniature golfing and throws a fit after Brad gets a hole-in-one.
Wes Davidson, the president of Binford, makes Tim promote a bad tool on Tool Time. Meanwhile, the boys go shopping and find a way to save money.
The boys buy a remote controlled car with stock bonds from their grandmother.
On Thanksgiving, for a perfect Christmas card, Tim builds a Christmas Village and has the family wear costumes.
At their high school reunion, Jill tries to avoid Joanie Graham, her high school friend who stole her boyfriend, and Tim and Jack try to fix the amplifier. Meanwhile, Al watches the boys and Brad's girlfriend Ashley.
Tim tries to beat Doc Johnson in the neighborhood Christmas light contest, but Randy is leaking information to Doc's granddaughter. Brad wants to go skiing with Tom Wheeler's family on Christmas.
Randy loses a sled race to Vinnie. But after following Tim's advice of racing Vinnie again with a better sled, Randy sprains his arm. Meanwhile, Brad contemplates stopping his saxophone lessons.
Al doesn't want to come to dinner with the Taylors after Ilene has a dream about Tim riding on a golden stallion in tight bicycle shorts.
When Jill is having Ilene and Marie over, Tim goes fishing with Al to get out of the house.
Jill feels bad when her father, the army colonel, asks her opinion on his boring book. Meanwhile, Tim builds a hockey puck shooter when Randy becomes a goalie.
Tim has Randy move into Mark's room when Randy bothers Brad on the phone.
Jill joins Al's team for Habitat for Humanity because Tim thinks married couples shouldn't work together. Meanwhile, Brad finds a locket and gives it to Ashley but finds out it was Marie's.
When Irma can't host her show (Cooking with Irma) for a week, she asks Al to fill-in as host and Tim to be his assistant. Tim has a hard time not being the centre of attention, but when Jill shows him that he can assist her, he decides to continue to help Al. Meanwhile, Randy finds it hard to talk to a girl in his class named Beth.
After Tim charms all the women at a baby shower, Jill wants a romantic evening with him, but Tim takes the boys to a Demolition Derby.
Tool Time doesn't have enough money for a big fifth anniversary show, so Tim shows a clip of the first episode.
Tim and the boys plan on getting Jill a hot tub for Mother's Day and getting rid of the swing set. But they find the swing set meant more to Jill than they thought and she wants an herb garden instead of a hot tub.
After researching cosmetic surgery on the computer, Jill finds that Tim wants her to have cosmetic surgery. Meanwhile, Tim plays a computer game with the boys and the loser must clean the house.
Randy, pretending to be thirty-two years old, meets a woman on a singles message board on the computer, and she comes by for a visit. Meanwhile, Tim tries to help Mark with his science project.
After Bob Vila raises more money than Tim for Jill's library fundraiser, Tim challenges him to a race... in his unfinished hot rod.